Gwynedd & Powys
Gruffydd reappeared on the scene years later, having escaped from captivity. According to his biography he was in fetters in the market-place at Chester when Cynwrig the Tall on a visit to the city saw his opportunity when the burgesses were at dinner. He picked Gruffydd up, fetters and all, and carried him out of the city on his shoulders. There is debate among historians as to the yeare of Gruffydd's escape. Ordericus Vitalis mentions a "Grifridus" attacking the Normans in 1088. The History in one place states that Gruffydd was imprisoned for twelve years, in another that he was imprisoned for sixteen years. Since he was captured in 1081, that would date his release to 1093 or 1097. Gruffydd again took refuge in Ireland but returned to Gwynedd to lead the assaults on Norman castles such as Aber Lleiniog.
The Welsh revolt had begun in 1094 and by late 1095 had spread to many parts of Wales. This induced William II of England (William Rufus) to intervene, invading nothern Wales in 1095. However his army was unable to the Welsh to battle and returned to Chester without having achieved very much. King Willam mounted a second invasion in 1097, but again without much success. The History only mentions one invasion by Rufus, which could indicate that Gruffydd did not feature in the resistance to the first invasion. At this time Cadwgan ap Bleddyn of Powys led the Welsh resistance. In the summer of 1098 Earl Hugh of Chester joined with Earl Hugh of Shrewsbury in another attempt to recover his losses in Gwynedd. Gruffydd and his ally Cadwgan ap Bleddyn retreated to Anglesey, but then were forced to flee to Ireland in a skiff when a fleet he had hired from the Danish settlement in Ireland accepted a better offer from the Normans and changed sides.
The situation was changed by the arrival of a Norwegian fleet under the command of King Magnus III of Norway, also known as Magnus Barefoot, who attacked the Norman forces near the eastern end of the Menai Straits. Earl Hugh of Shrewsbury was killed by an arrow said to have been shot by Magnus himself. The Normans were obliged to evacuate Anglesey, and the following yeare Gruffydd returned from Ireland to take possession again, having apparently come to an agreement with Earl Hugh of Chester. With the death of Hugh of Chester in 1101 Gruffydd was able to consolidate his position in Gwynedd, as much by diplomacy as by force. He met King Henry I of England who granted him the rule of Llyn, Eifionydd, Ardudwy and Arllechwedd, considerably extending his kingdom. By 1114 he had gained enough power to induce King Henry to invade Gwynedd in a three-pronged attack, one detachment led by King Alexander I of Scotland. Faced by overwhelming force, Gruffydd was obliged to pay homage to Henry and to pay a heavy fine, but lost no territory.
By about 1118 Gruffydd's advancing years meant that most of the fighting which pushed Gwynedd's borders eastward and southwards was done by his three sons by his wife Angharad, daughter of Owain ab Edwin, Cadwallon, Owain Gwynedd and later Cadwaladr. The cantrefs of Rhos and Rhufoniog were annexed in 1118, Meirionnydd captured from Powys in 1123 and Dyffryn Clwyd in 1124. Another invasion by the king of England in 1121 was a military failure. The king had to come to terms with Gruffydd and made no further attempt to invade Gwynedd during Gruffydd's reign. The death of Cadwallon in a battle against the forces of Powys near Llangollen in 1132 checked further expansion for the time being. Gruffydd was now powerful enough to ensure that his nominee, David the Scot was consecrated as Bishop of Bangor in 1120. The see had been effectively vacant since Bishop Hervey had been forced to flee by the Welsh almost twenty years before, since Gruffydd and King Henry could not agree on a candidate. David went on to rebuild Bangor Cathedral with a large financial contribution from Gruffydd. Owain and Cadwaladr in alliance with Gruffydd ap Rhys of Deheubarth gained a crushing victory over the Normans at Crug Mawr near Cardigan in 1136 and took possession of Ceredigion. The latter part of Guffydd's reign was considered to be a "Golden Age"; according to the Life of Gruffydd ap Cynan Gwynedd was "bespangled with lime-washed churches like the stars in the firmament".
Gruffydd died in his bed, old and blind, in 1137 and was mourned by the annalist of Brut y Tywysogion as the head and king and defender and pacifier of all Wales. He was buried by the high altar in Bangor Cathedral which he had been involved in rebuilding. He also made bequests to many other churches, including one to Christ Church Cathedral, Dublin where he had worshipped as a boy. He was succeeded as king of Gwynedd by his son Owain Gwynedd. His daughter, Gwenllian, who married Gruffydd ap Rhys of Deheubarth, son of his old ally Rhys ap Tewdwr, is also notable for her resistance to English rule.